JPH0768326B2 - Method for manufacturing urethane lens resin - Google Patents

Description

TECHNICAL FIELD The present invention relates to a method for producing a urethane lens resin having good optical properties and heat resistance.

[Conventional technology]

Since plastic lenses are lighter in weight and less likely to break than inorganic lenses and can be dyed, they have rapidly become popular in optical elements such as spectacle lenses and camera lenses in recent years.

As the resin currently widely used for these purposes, diethylene glycol bis (allyl carbonate) (hereinafter,
There is one that radically polymerizes (called DAC). This resin has various characteristics such as excellent impact resistance, light weight, excellent dyeability, and good machinability such as machinability and abrasiveness. There is.

However, the refractive index of this resin is an inorganic lens (n _D = 1.
Compared with 52), n _D = 1.50, which is small, and it is necessary to increase the center thickness, edge thickness, and curvature of the lens in order to obtain optical characteristics equivalent to those of a glass lens. Inevitable. Therefore, a resin for lenses having a higher refractive index is desired.

Furthermore, as one of the lens resins that give a high refractive index,
Reaction of an isocyanate compound with a hydroxy compound such as diethylene glycol (JP-A-57-136601) or reaction with a hydroxy compound containing a halogen atom such as tetrabromobisphenol A (JP-A-58-16461).
There is known a polyurethane resin obtained by a reaction with 5) or a hydroxy compound having a diphenyl sulfide skeleton (JP-A-60-194401).

Further, the applicant of the present invention has found that, as a resin for a high refractive index lens, it reacts with an isocyanate compound and a hydroxy compound containing a sulfur atom (JP-A-60-217229), and further with a polythiol compound (JP-A-60-217229). 60-199016, 62-26731
We have previously proposed a plastic lens made of polyurethane resin, etc.

However, these known resins have a refractive index higher than that of a resin using DAC, but are still insufficient, or a compound having a large number of halogen atoms or aromatic rings in the molecule in order to improve the refractive index. Therefore, it has the drawbacks of poor weather resistance and large specific gravity.

Further, even in the plastic lens resin proposed by the present inventors, the refractive index is still insufficient, or the dispersion is large relative to the refractive index of glass, and the heat resistance in post-processing such as dyeing and coating is insufficient. However, there are problems such as that, and further improvement is desired.

[Problems to be solved by the invention]

An object of the present invention is to solve the above problems and provide a urethane lens having a higher refractive index, an extremely low dispersion, excellent heat resistance and weather resistance, a light weight, and excellent impact resistance. .

[Means for Solving the Problems]

In view of such circumstances, as a result of further investigations by the present inventors, a certain alicyclic isocyanate compound is reacted with an active hydrogen compound selected from a polyol compound, a polythiol compound and a thiol compound having a hydroxyl group. As a result, the inventors have found that a urethane-based resin for lenses having a high refractive index, an extremely low dispersion, excellent heat resistance and weather resistance, a light weight, and excellent impact resistance is obtained, and the present invention has been completed.

That is, the present invention relates to an alicyclic isocyanate compound represented by the formula (I) and / or an alicyclic isocyanate compound represented by the formula (II), Manufacture of a urethane lens resin having a high refractive index and low dispersion obtained by reacting a polyol compound, a polythiol compound and a thiol compound having a hydroxyl group, excellent heat resistance, weather resistance, light weight and excellent impact resistance It is about the method.

The alicyclic isocyanate compound represented by formula (I) used in the present invention is specifically 2,5-bis (isocyanatomethyl) bicyclo [2,2,1] heptane 2,6-bis (Isocyanatomethyl) bicyclo [2,2,1] heptane, and the alicyclic isocyanate compound represented by the formula (II) is specifically 3,8-bis (isocyanatomethyl) tricyclo [5 , 2,1,0 ^2.6 ) decane, 3,9-bis [isocyanatomethyl] tricyclo [5,2,1,0 ^2.6 decane], 4,8-bis [isocyanatomethyl] tricyclo [5,2,1 , 0 ^2.6 ] decane and 4,9-bis [isocyanatomethyl] tricyclo [5,2,1,0 ^2.6 ] decane. These may be used alone or in combination of two or more.

The polyol compound used in the present invention is a bifunctional or higher functional polyol, and also includes a compound having a sulfur atom in the molecule.

Specifically, as the bifunctional or higher functional polyol, for example,
Ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, dipentaerythritol, tripentaerythritol , Sorbitol, erythritol, threitol,
Ribitol, arabinitol, xylitol, altitol, mannitol, dorsitol, iditol, glycol, inositol, hexanetriol, triglycerose, diglycerol, triethylene glycol, polyethylene glycol, tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentane. diol, cyclohexane diol, cycloheptane diol, cyclooctane diol, cyclohexane dimethanol, hydroxypropyl cyclohexanol, tricyclo [5,2,1,0 ^2.6] decane - dimethanol, bicyclo [4,3,0] nonanediol, di Cyclohexanediol, tricyclo [5,3,1,1] dodecanediol, bicyclo [4,3,0] nonanedimethanol, tricyclo [5,3,1,1] dodecane-diethanone , Hydroxypropyltricyclo [5,3,1,1] dodecanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1-bicyclohexylidenediol, cyclohexanetriol, maltitol, lactitol, dihydroxynaphthalene, Trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl) pyrogallol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, di (2-hydroxyethoxy) benzene, bisphenol A-bis (2-hydroxyethyl ether), tetrabromobisphenol A, tetrabromobisphenol A-bis (2-hydroxyethyl ether) Ter), dibromoneepentyl glycol, and epoxy resin, as well as oxalic acid, glutamic acid, adipic acid, acetic acid, propionic acid, cyclohexanecarboxylic acid, β-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid A condensation reaction product of an organic polybasic acid such as 3-bromopropionic acid, 2-bromoglycolic acid, dicarboxycyclohexane, pyromellitic acid, butanetracarboxylic acid, and bromophthalic acid with the polyol, the polyol and ethylene oxide, Examples thereof include addition reaction products with alkylene oxides such as propylene oxide and addition reaction products with alkylene polyamines and alkylene oxides such as ethylene oxide and propylene oxide.

Further, halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds may be used. These may be used alone or in combination of two or more.

Examples of the bifunctional or higher functional polyol containing a sulfur atom include bis [4- (hydroxyethoxy) phenyl] sulfide, bis [4- (2-hydroxypropoxy) phenyl] sulfide, bis [4- (2, 3-dihydroxypropoxy) phenyl] sulfide, bis [4
-(4-hydroxycyclohexyloxy) sulfide,
Bis [2-methyl-4 (hydroxyethoxy) -6-butylphenyl] sulfide and compounds obtained by adding ethylene oxide and / or propylene oxide having an average of 3 molecules or less per hydroxyl group to these compounds, di (2-
Hydroxyethyl) sulfide, 1,2-bis (2-hydroxyethylmercapto) ethane, bis (2-hydroxyethyl) disulfide, 1,4-dithiane-2,5-diol, bis (2,3-dihydroxypropyl) sulfide ,
Tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (trade name bisphenol S), tetrabromobisphenol S,
Tetramethylbisphenol S, 4,4'-thiobis (6
-Tert-butyl-3-methylphenol), 1,3-bis (2-hydroxyethylthioethyl) -cyclohexane and the like.

Further, halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds may be used. These may be used alone or in combination of two or more.

Further, the polythiol compound used in the present invention is a polythiol having two or more functional groups, and includes those containing at least one sulfur atom in addition to the mercapto group.

Specifically, as the bifunctional or higher polythiol, for example, methanedithiol, 1,2-ethanedithiol, 1,1-
Propanedithiol, 1,2-Propanedithiol, 1,3-
Propanedithiol, 2,2-Propanedithiol, 1,6-
Hexanedithiol, 1,2,3-propanetrithiol,
1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol , Bicyclo 〔2,
2,1] peptor exo-cis-2,3 dithiol, 1,1-bis (mercaptomethyl) cyclohexane, thiomalic acid bis (2-mercaptoethyl ester), 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester) ), 2,3
-Dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol (3-mercaptoacetate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1 , 2-Dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2 −
Mercaptoacetate), ethylene glycol bis (3
-Mercaptopropionate), trimethylolpropane bis (2-mercaptoacetate), trimethylolpropane bis (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropioate) Nate) and other aliphatic polythiols, and halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds thereof, 1,
2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl)
Benzene, 1,4-bis (mercaptomethyl) benzene,
1,2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2-bis (mercaptomethyleneoxy) benzene, 1,3-bis (Mercaptomethyleneoxy) benzene, 1,4-bis (mercaptomethyleneoxy) benzene, 1,2-bis (mercaptoethyleneoxy) benzene, 1,3-bis (mercaptoethyleneoxy) benzene, 1,4-bis (mercapto Ethyleneoxy) benzene, 1,2,3-trimercaptobenzene, 1,2,4
-Trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,
3,5-tris (mercaptomethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris (mercaptoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 1,2,3-Tris (mercaptomethyleneoxy) benzene, 1,2,4-tris (mercaptomethyleneoxy) benzene, 1,3,5-tris (mercaptomethyleneoxy) benzene, 1,2,3-tris ( Mercaptoethyleneoxy) benzene, 1,2,4-tris (mercaptoethyleneoxy) benzene, 1,3,5-tris (mercaptoethyleneoxy) benzene, 1,2,3,4-tetramercaptobenzene, 1,2, 3,5-tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1,2,
3,4-Tetrakis (mercaptomethyl) benzene, 1,2,
3,5-tetrakis (mercaptomethyl) benzene, 1,2,
4,5-Tetrakis (mercaptomethyl) benzene, 1,2,
3,4-Tetrakis (mercaptoethyl) benzene, 1,2,
3,5-Tetrakis (mercaptoethyl) benzene, 1,2,
4,5-Tetrakis (mercaptoethyl) benzene, 1,2,
3,4-Tetrakis (mercaptomethyleneoxy) benzene, 1,2,3,5-Tetrakis (mercaptomethyleneoxy) benzene, 1,2,4,5-Tetrakis (mercaptomethyleneoxy) benzene, 1,2,3, 4-tetrakis (mercaptoethyleneoxy) benzene, 1,2,3,5-tetrakis (mercaptoethyleneoxy) benzene, 1,2,4,5-tetrakis (mercaptoethyleneoxy) benzene, 2,
2'-dimercaptobiphenyl, 4,4'-dimercaptobiphenyl, 4,4'-dimercaptobibenzyl, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,4-naphthalenedithiol, 1,5 -Naphthalenedithiol, 2,6-
Naphthalenedithiol, 2,7-naphthalenedithiol,
2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracene dimethanethiol, 1,3-di (p-methoxyphenyl)
Aromatic polythiols such as propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (p-mercaptophenyl) pentane, and 2 , 5-Dichlorobenzene-1,3
-Dithiol, 1,3-di (p-chlorophenyl) propane-2,2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2,3,4,6-tetrachloro-1,5 -Chlorine-substituted aromatic polythiols such as chlorinated compounds such as bis (mercaptomethyl) benzene and bromine-substituted compounds, and 2-
Methylamino-4,6-dithiol-sym-triazine, 2
-Ethylamino-4,6-dithiol-sym-triazine,
2-amino-4,6-dithiol-sym-triazine, 2-
Morpholino-4,6-dithiol-sym-triazine, 2-
Cyclohexylamino-4,6-dithiol-sym-triazine, 2-methoxy-4,6-dithiol-sym-triazine, 2-phenoxy-4,6-dithiol-sym-triazine, 2-thiobenzeneoxy-4,6 -Dithiol -sym-
Examples thereof include polythiols containing a heterocycle such as triazine and 2-thiobutyloxy-4,6-dithiol-sym-triazine, and halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds thereof.

Each of them may be used alone or in combination of two or more.

Examples of the bifunctional or higher polythiol containing at least one sulfur atom in addition to the mercapto group include, for example, 1,2
-Bis (mercaptomethylthio) benzene, 1,3-bis (mercaptomethylthio) benzene, 1,4-bis (mercaptomethylthio) benzene, 1,2-bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethyl) Thio) benzene, 1,4-bis (mercaptoethylthio)
Benzene, 1,2,3-Tris (mercaptomethylthio) benzene, 1,2,4-Tris (mercaptomethylthio) benzene, 1,3,5-Tris (mercaptomethylthio) benzene, 1,2,3-Tris (mercapto) Ethylthio) benzene, 1,2,4-tris (mercaptoethylthio) benzene, 1,3,5-tris (mercaptoethylthio) benzene, 1,2,3,4-tetrakis (mercaptomethylthio) benzene, 1, 2,3,5-tetrakis (mercaptomethylthio) benzene, 1,2,4,5-tetrakis (mercaptomethylthio) benzene, 1,2,3,4-tetrakis (mercaptoethylthio) benzene, 1,2,3, Aromatic polythiols such as 5-tetrakis (mercaptoethylthio) benzene, 1,2,4,5-tetrakis (mercaptoethylthio) benzene, and their nuclear alkylated products, bis (mercaptomethyl) sulfur , Bis (mercaptoethyl) sulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) methane, bis (3-mercaptopropylthio) methane, 1,2-bis ( Mercaptomethylthio) ethane, 1,2-bis (2-mercaptoethylthio) ethane,
1,2-bis (3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2
-Mercaptoethylthio) propane, 1,3-bis (3-
Mercaptopropylthio) propane, 1,2,3-tris (mercaptomethylthio) propane, 1,2,3-tris (2-mercaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane , Tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1 , 4-dithiane, bis (mercaptomethyl)
Disulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) disulfide, etc., and their esters of thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate) Pionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate) ), Hydroxymethyl disulfide bis (2-mercaptoacetate),
Hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis (2-mercaptoacetate), hydroxypropyl Disulfide bis (3-
Mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4-dithiane, 2,5-diol bis (2-mercaptoacetate) ), 1,4-dithiane-2,5-diol bis (3-mercaptopropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodipropionic acid bis (2-mercaptoethyl ester), 4, Four
-Thiodibutyric acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropionic acid bis (2-mercaptoethyl ester), 4,4-dithiodiphtylic acid bis (2-mercaptoethyl ester) Ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercaptopropyl ester), dithioglycolic acid bis (2,3-dimethylcaptopropyl ester), Bis (dithiodipropionate) (2,
Examples thereof include aliphatic polythiols such as 3-dimercaptopropyl ester) and heterocyclic compounds such as 3,4-thiophenedithiol and bismuthiol.

Further, halogen-substituted compounds such as chlorine-substituted compounds and bromine-substituted compounds may be used. These may be used alone or in combination of two or more.

Further, the thiol compound having a hydroxy group used in the present invention includes a compound containing at least one sulfur atom in addition to the mercapto group.

Specifically, for example, 2-mercaptoethanol, 3-
Mercapto-1,2-propanediol, glycerin di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,7-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2 -Propanol, 1,3
-Dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris (3-mercaptopropionate), pentaerythritol mono (3
-Mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), pentaerythritol pentakis (3-mercaptopropionate),
Hydroxymethyl-tris (mercaptoethylthiomethyl) methane, 1-hydroxyethylthio-3-mercaptoethylthiobenzene, 4-hydroxy-4'-mercaptodiphenyl sulfone, 2- (2-mercaptoethylthio) ethanol, dihydroxyethyl sulfide Mono (3-mercaptopropionate), dimercaptoethane mono (sulfylate), hydroxyethylthiomethyl-tris) mercaptoethylthiomethyl) methane and the like can be mentioned.

Further, halogen-substituted products of these chlorine-substituted products and bromine-substituted products may be used. These may be used alone or in combination of two or more.

These active hydrogen compounds and the formula (I) and / or the formula (II)
The usage ratio of the alicyclic isocyanate compound represented by
The functional group molar ratio of NCO / (SH + OH) is usually in the range of 0.5 to 3.0, preferably in the range of 0.5 to 1.5.

The urethane lens resin of the present invention is mainly composed of a urethane bond and / or a thiocarbamic acid S-alkyl ester bond by an isocyanate group and a hydroxy group and / or a mercapto group, but depending on the purpose, other than that, an alohanate bond. Of course, it does not matter if it contains a urea bond, a biuret bond, or the like. For example, it is often the case that the urethane bond or the thiocarbamic acid S-alkyl ester bond is further reacted with an isocyanate group to increase the crosslink density. In this case, the reaction rate is increased to at least 100 ° C. or higher and a large amount of isocyanate component is used. Alternatively, an urea bond or a biuret bond can be used by partially using an amine or the like.

When using a compound other than a polyol compound, a polythiol compound, or a thiol compound having a hydroxy group, which reacts with an isocyanate compound, it is necessary to pay particular attention to coloring.

Further, depending on the purpose, as in the known molding method, various substances such as a chain extender, a cross-linking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, an oil-soluble dye, and a filler may be added. Good.

To adjust the desired reaction rate, thiocarbamic acid S
-A known reaction catalyst used in the production of alkyl ester or polyurethane may be appropriately added.

The lens resin of the present invention is usually obtained by cast polymerization.

Specifically, at least one active hydrogen selected from the alicyclic isocyanate compound represented by the formula (I) and / or the formula (II), a polyol compound, a polythiol compound and a thiol compound having a hydroxy group. Compounds are mixed. This mixture is defoamed by a suitable method, if necessary, and then poured into a mold, and usually heated gradually from a low temperature to a high temperature for polymerization.

The urethane lens resin of the present invention thus obtained has a high refractive index and low dispersion, excellent heat resistance and weather resistance, and has features of being lightweight and excellent in impact resistance. It is suitable as a material for optical elements such as camera lenses.

Further, the lens made of the urethane resin of the present invention is
In order to improve antireflection, high hardness, abrasion resistance, chemical resistance, antifogging property, fashionability, etc. as necessary, surface polishing, antistatic treatment, hard coat treatment, antireflection coat Physical or chemical treatment such as treatment, dyeing treatment, and light control treatment can be performed.

〔Example〕

Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. In the performance test of the obtained lens resin, the refractive index, Abbe number, weather resistance, heat resistance and appearance were evaluated by the following test methods.

-Refractive index, Abbe number: Measured at 20 ° C using a Pulfrich refractometer.

・ Weather resistance: Set the lens resin to a weather odometer equipped with a sunshine carbon arc lamp and set it to 200
After a lapse of time, the lens was taken out and the hue was compared with that of the lens resin before the test. The evaluation criteria were no change (◯), slight yellowing (Δ) and yellowing (x).

・ Heat resistance: Using a thermomechanical analyzer [Perkin Elmer (USA)], weigh 5 g on the test piece at 2.5 ° C.
The temperature was started at a heating rate of 1 / min to measure the thermal deformation start temperature.

・ Appearance: Visual observation.

Example 1 2,5-bis (isocyanatomethyl) bicyclo [2,2,1]
40 g of a (1: 1) mixture of heptane and 2,6-bis (isocyanatomethyl) bicyclo [2,2,1] heptane was mixed with 42.8 g of tetrakis (2-mercaptoethylthiomethyl) methane to give dibutyltin dilaurate. After adding 0.08 g to make the mixture uniform, the mixture was poured into a mold made of a glass mold and a gasket and cured by heating.

The resin thus obtained is colorless and transparent and has excellent weather resistance, a refractive index n _D = 1.62, an Abbe number ν _D = 42, and a thermal deformation starting temperature of 12
It was 0 ° C.

Example 2 3,8-bis (isocyanatomethyl) tricyclo [5,2,
1,0 ^2.6 ] decane, 3,9-bis (isocyanatomethyl)
Tricyclo [5,2,1,0 ^2.6 ] decane, 4,8-bis (isocyanatomethyl) tricyclo [5,2,1,0 ^2.6 ] decane, 4,
9-bis (isocyanatomethyl) tricyclo [5,2,1,0
^2.6 ] Mix 47.8 g of a (1: 1: 1: 1) mixture of decane and 42.8 g of tetrakis (2-mercaptoethylthiomethyl) methane, add 0.09 g of dibutyltin dilaurate and homogenize it, then add a glass mold and a gasket. It was poured into a mold made of, and cured by heating.

The resin thus obtained is colorless and transparent and has excellent weather resistance, a refractive index n _D = 1.62, an Abbe number ν _D = 41, and a thermal deformation starting temperature of 125.
It was ℃.

Examples 3 to 8 and Comparative Examples 1 to 2 Resins having the compositions shown in Table 1 were synthesized in the same manner as in Examples 1 and 2, and the evaluation results are shown in Table 1.

Claims (1)

[Claims] 1. An alicyclic isocyanate compound represented by formula (I) and / or an alicyclic isocyanate compound represented by formula (II), A method for producing a urethane lens resin, which comprises mixing at least one active hydrogen compound selected from a polyol compound, a polythiol compound and a thiol compound having a hydroxy group, and curing the mixture by heating.